Regioselective addition of organomagnesium reagents to N-silyl activated nicotinic acid esters-a convenient method for the synthesis of 4,4-disubstituted 1,4-dihydronicotinates

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Abstract

The addition of RMgX or R2Mg to nicotinic acid esters, activated with triisopropylsilyl triflate, was investigated. The regioselectivity of this reaction, where 4-unsubstituted and 4-substituted pyridine derivatives were employed as starting materials, was examined. Depending on the structure of the organomagnesium reagent varying ratios of 1,2-, 1,4-, and 1,6-regioisomers were obtained but in any case the 1,4-addition products were clearly predominating. Desilylation of the isomeric pure addition products with LiOH provided stable 4,4-disubstituted dihydropyridines, which could be easily N-alkylated with alkylhalides in high yield. Furthermore, it was shown that the silyl protecting group of the obtained dihydropyridines can be easily replaced by an acyl group. © 2009 Elsevier Ltd. All rights reserved.

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Sperger, C. A., & Wanner, K. T. (2009). Regioselective addition of organomagnesium reagents to N-silyl activated nicotinic acid esters-a convenient method for the synthesis of 4,4-disubstituted 1,4-dihydronicotinates. Tetrahedron, 65(29–30), 5824–5833. https://doi.org/10.1016/j.tet.2009.05.008

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